Ross Ulbricht allegedly ordered six, not two, executions and kept a detailed journal while running his online drug empire Silk Road under the alias "Dread Pirate Roberts," according to a new court filing by the U.S. government.
Federal prosecutor Serrin Turner revealed compelling new details about the case the government is building against Ulbricht, 29, in a letter submitted Wednesday evening opposing Ulbricht's request for bail. Turner further discussed the new findings during a hearing Thursday, during which a federal judge ordered Ulbricht to be held without bail.
See also: Silk Road Reborn: There's a New Dread Pirate Roberts
"It wasn't just online talk; it wasn't just pretend," Turner said. "Just because it was on the computer doesn't make it any less of a crime."
The government has three main sources of information in this case, according to Turner. While Silk Road was operational, the FBI obtained images of the site's server and gained access to the private communications of all users, including Dread Pirate Roberts. The other source is Ulbricht's personal laptop.
FBI agents seized the laptop during Ulbricht's arrest at the Glen Park branch of the San Francisco Public Library on Oct. 1. The agency has been conducting forensic analysis of the device ever since.
The first thing agents noted, however, was that Ulbricht was signed into Silk Road as Dread Pirate Roberts at the time of his arrest, according to Turner's filing. The U.S. attorney's office provided screen shots of Ulbricht's laptop at the library that show he was on an administrator's page on Silk Road, addressing users' support requests.

Other screenshots show that Ulbricht was logged into his computer with the username "Frosty," and he used an encrypted chat program with the username "Dread" and an avatar that matched Silk Road owner "Dread Pirate Roberts."
Ulbricht allegedly used the moniker "Frosty" to post about Silk Road's source code web development forums. Additionally, Turner said analysis of the Silk Road server showed that the only user with direct access to it was someone with the username "Frosty."
Analysis of Ulbricht's laptop also revealed several documents detailing the rise of Silk Road, including a journal, financial spreadsheets and an activity log. The U.S. attorney's recent federal filing excerpts one of the initial journal entries from 2010.
I began working on a project that had been in my mind for over a year. I was calling it Underground Brokers, but eventually settled on Silk Road. The idea was to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them.
Ulbricht allegedly documented his struggles and aspirations in this journal, writing that he wasn't able to create the site by the end of 2010, but he was hopeful that, in 2011, he would be "creating a year of prosperity and power beyond what [he has] ever experienced before." It went on: "Silk Road is going to become a phenomenon and at least one person will tell me about it, unknowing that I was its creator."
The journal also is said to describe how Ulbricht grew several "several kilos of high-quality schrooms" in a log cabin so he would have something to sell on the website when it opened. The prosecution also described a spreadsheet on Ulbricht's computer titled "NetWorthCalculator," on which he valued Silk Road at $104 million.
In addition to the journal and spreadsheet, the court filing mentions a computer file titled "log" that Ulbricht supposedly used to keep track of his action as Dread Pirate Roberts throughout 2013. The document reportedly contains entries such as "withdrawals all caught up" and "switched to direct connect for bitcoin instead of over ssh portforward."
The U.S. attorney also writes of more menacing entries to Ulbricht's "log" file, including "being blackmailed with user info. talking with large distributor (hell's angels)," "commissioned hit on blackmailer with angels" and "got word that blackmailer was executed.
At the time of Ulbricht's arrest, the FBI documented two alleged instances of him ordering executions. One of the two was staged by the FBI, and the other involved a still-mysterious scenario.
Wednesday's court filing revealed four new charges of murder-for-hire requests, none of which appear to have resulted in death. If you're counting, that's six times Ulbricht supposedly ordered executions which resulted in no known deaths. The U.S. attorney's court filing states that Ulbricht paid a total of $730,000 for these hits through wire and Bitcoin transfers.
The newly revealed four execution requests stem from the aforementioned mysterious hit that did not appear to produce a death. In that instance, a Silk Road user named "FriendlyChemist" tried to extort $500,000 from Dread Pirate Roberts by threatening to reveal thousands of Silk Road users' real-life identities.
See also: Exclusive: Inside the World of a Silk Road Drug Dealer
Court documents state that Ulbricht paid another Silk Road user named "redandwhite" $150,000 to kill FriendlyChemist. Though redandwhite supposedly produced photo evidence of the murder, Canadian authorities had no knowledge of the person said to have been killed, and there were no reported homicides in the area during the time of the alleged hit.
Wednesday's filing states that redandwhite went back to Dread Pirate Roberts after supposedly killing FriendlyChemist and said, before his death, FriendlyChemist implicated another Silk Road user named "tony76" in the blackmail scam.
Redandwhite then offered to kill tony76 but claimed he wouldn't be able to do it without also killing three other people with whom tony76 lived and worked. Ulbricht supposedly responded, "hmm... ok, I'll defer to your better judgement and hope we can recover some assets from them," and they settled on a price of $500,000 for the job.
While Canadian authorities found no evidence that these murders ever occurred, the FBI did, however, find proof that Ulbricht paid for the murders, according to the agency's court filings.
In addition to the letter opposing Ulbricht's bail request, the U.S. attorney's office released several other documents Wednesday, including a partially complete citizenship application for Dominica, a small island nation in the Caribbean.
Turner, the prosecuting attorney, said Ulbricht had "an emergency to-do list on his computer" and he had looked into obtaining dual citizenship. Several weeks before Ulbricht's arrest, Department of Homeland Security agents questioned him at his San Francisco residence about a package they intercepted containing fake photo IDs.
"The evidence, in the government's opinion, is absolutely overwhelming," Turner said, discussing these new revelations before a federal judge at Thursday's hearing.
Ulbricht's defense attorney Joshua Dratel said he didn't receive the government's filing regarding the new details until 7:30 p.m. Wednesday, which didn't leave him enough time to fully consider the information. Even so, Dratel declined the judge's offer to delay the bail hearing.
"There's no proof that any of this occurred," Dratel said.
The proof was substantial enough for the judge to deny Ulbricht's considerable bail request. Family and friends offered to pledge more than $1 million on Ulbricht's behalf, and nearly two dozen people offered to co-sign a bond.
Chief U.S. Magistrate Judge Kevin Fox said there is "clear and convincing" evidence that Ulbricht would be a danger if freed. Also, the FBI has not been able to recover the majority of the millions of dollars worth of Bitcoin Ulbricht is thought to be harboring. Fox referenced this money, saying Ulbricht "has the means to flee."
Ulbricht is due back in court next month.
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Image: U.S. Department of Justice